The Cars of the Real-Life Story of “Black Mass”

The movie Black Mass had its premiere in Boston last night, and opens in nationwide this week. It’s based on the book of the same name which depicts the life and crimes of convicted murderer James “Whitey” Bulger. Crime scene photos released during Bulger’s trial show a cross-section of 1970s and early 1980s cars.

In Boston, Whitey Bulger was a fixture in the local news throughout the late 1970s and into the 1990s until he went underground on December 23, 1994. He became something of a folk hero during that time, but in 2001, Dick Lehr and Gerard O’Neill detailed the horror of his crimes in their book Black Mass, and the evidence that the FBI had been using him as an informant, and looked the other way while he was committing them.

It’s a story cast with actual crooks, villains, drug pushers and murderers, set against the backdrop of Boston, Massachusetts at its most scuzzy and lawless.

After he was finally captured in 2011, evidence photos made the rounds and they reveal a lot of what gangsters, businessmen and ordinary folks caught in the crossfire were driving. We’ve married those photos up with the photos available from IMCdB to see just how close the casting agencies that provided the cars got to full authenticity.

One interesting thing to note is that in about 2/3s of these photographs, the cars all seem to be shod with Sears RoadHandler snow tires. These guys may have been safe crackers, IRA gun smugglers and hit men, but they appreciated winter traction.

Bulger’s main hangout at the time was Lancaster Foreign Motors, which doubled as the headquarters for Boston’s vicious Winter Hill Gang. The biggest tipoff for the FBI — if it wasn’t actually involved in covering Bulger’s criminal activity — should have been that there were hardly any foreign motors at Lancaster Foreign Motors. Here, Bulger and his band of thugs are hanging around a 1979 Buick Riviera.
Lancaster Foreign Motors was located on Lancaster Street in Boston’s North End. Bulger (right) leans up against a 1979 Chevrolet Caprice here.
In this screen capture from the movie, Johnny Depp as Whitey Bulger emerges from an Oldsmobile Ninety-Eight, rather than a Caprice. For the era, the Ninety-Eight is right on the money, but the evidence photos show that Whitey would be riding around in something a little less obvious.

The car belonged to Michael Milano, an innocent bartender who was giving two friends a ride home. Milano was killed at the wheel. John “The Executioner” Martorano testified that he and the Winter Hill Gang opened fire on the car with machine guns because they had mistaken the identity of the people in the car.

This 1973 Buick Century was Frank Capizzi’s ride home on March 19, 1973. Capizzi was on the way to through the North End when a hail of gunfire hammered the Buick, injuring Capizzi and decapitating one of the passengers along for the ride.

“I was hit in the head and could feel warm blood running down my neck,” the 78-year-old testified in his testimony at Bulger’s trial.

Unlike Milano, Capizzi was no innocent bystander. His partner was “Indian Al” Notarangeli, an extortionist putting the squeeze on Boston mafia don Gennaro Angiulo. Both the driver and front passenger in the Century were killed in the attack.

There’s definitely a Buick in one of the crime scenes in the movie, but it’s tough to tell if it’s a Century, or if the scene is depicting Frank Capizzi’s Wild Ride.

One of the screen captures from Black Mass shows the result of such an attack, but the car is a Colonnade-era Chevrolet Malibu.

Bulger and his gang’s crimes weren’t limited to just hit men and bartenders. Roger Wheeler appeared to be the straightest of straight arrows. He was the former chairman of Telex Corporation, a major manufacturer of hearing aids and other audio devices.

Wheeler was also the former owner of World Jai Alai. World Jai Alai was popular for about three weeks in the early 1980s, and its popularity was driven by the fact that it seemed to be invented to be a sport on which to gamble. Gambling generally equals some level of corruption and infestation by organized crime, but Wheeler literally gave his life trying to keep it at bay.

Wheeler was murdered in the parking lot of his Tulsa, Oklahoma country club on May 27, 1981 when at Bulger’s request, John Martorano (he of the mistakenly murdered bartender), wearing a fake beard and a paper bag over his hand, walked up to Wheeler’s car and shot Wheeler between the eyes. Wheeler was in the front seat of this 1981 Cadillac Sedan de Ville, as evidenced by the Cadillac script on the mirrors and the leather interior.

Background cars in the film adaptation of the book include the nearly ubiquitous G-body Malibu, a B-Body Buick LeSabre and the left rear quarter of a two-tone brown Dodge Ramcharger.

There’s an alternate view of the same scene that provides a better look at the Buick and the Ramcharger, along with a mid-1970s Ford LTD, and Chevrolet’s most notorious turd, the Citation:

William “Billy” O’Brien was a nice young man who spent four years in prison for beating a man to death in a drunken brawl. Upon his release, he immediately joined “Indian Al” Notarangeli’s gang.

In 1973, O’Brien was on Morrissey Boulevard in this car, which appears to be a 1970 Plymouth Sport Fury four-door hardtop, judging by the high-back bucket seats and the script on the fender. 1970 was the only year that a Sport Fury was offered in a four-door bodystyle.

In his testimony at Bulger’s trial, Martarano, acting under Bulger’s and Howie Winter’s orders, shot and killed O’Brien with a machine gun.

Avert your eyes from the Lincoln Mark IV for a moment, and notice the feet sticking out of the phone booth next to it.

Those belong to Eddie “The Bulldog” Connors, former U.S. Marine and a boxer who once slugged it out in the New England Middleweight Championships.

Connors owned two gin mills across the street from each other on Savin Hill Avenue in Dorchester, just south of Boston proper. According to testimony at trial, Bulger and Steven “The Rifleman” Flemmi gunned Connors down as he was speaking to another Winter Hill Gang cronie from this phone booth at a Texaco station on Morrissey Boulevard, which runs north-south, parallel to Route 93.

We’ve run a couple of stories now on how cars get cast in TV shows like the Breaking Bad follow-up Better Call Saul and Ted 2. The right cars make the movie experience that much more authentic. These stills from the movie — and there are a handful more at the Internet Movie Car Database — show that whoever cast the cars for the movie certainly had their eye on the correct era.